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Re: meet sb vs meet with sb

This context is strangge. If I was describing the itinerary of a holiday, I might say 'On the second day,I'm going to meet my best friend Tom in the evening'. But if I was talking to someone at work about what I'd be doing when I went home, I'd say 'I'm going to meet my best friend Tom this evening'.

Re: meet sb vs meet with sb

In more formal situations you "meet with" somebody to discuss particular issues.
"The supervisor will meet with staff to present the new guidelines for sick leave."
"President Obama will meet with the Prime Minister of ____ to discuss issues of mutual concern,"